EP1321148A1 - Cyclotetrasaccharide pour augmenter l'activité d'élimination d'oxygène actif - Google Patents

Cyclotetrasaccharide pour augmenter l'activité d'élimination d'oxygène actif Download PDF

Info

Publication number
EP1321148A1
EP1321148A1 EP02257948A EP02257948A EP1321148A1 EP 1321148 A1 EP1321148 A1 EP 1321148A1 EP 02257948 A EP02257948 A EP 02257948A EP 02257948 A EP02257948 A EP 02257948A EP 1321148 A1 EP1321148 A1 EP 1321148A1
Authority
EP
European Patent Office
Prior art keywords
plant
composition
active oxygen
cyclotetrasaccharide
oxygen eliminating
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP02257948A
Other languages
German (de)
English (en)
Other versions
EP1321148B1 (fr
Inventor
Kazuyuki Kabushiki Kaisha Hayashibara Oku
Michio Kabushiki Kaisha Hayashibara Kubota
Shigeharu Kabushiki Kaisha Hayashibara Fukuda
Toshio Kabushiki Kaisha Hayashibara Miyake
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hayashibara Seibutsu Kagaku Kenkyujo KK
Original Assignee
Hayashibara Seibutsu Kagaku Kenkyujo KK
Hayashibara Biochemical Laboratories Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hayashibara Seibutsu Kagaku Kenkyujo KK, Hayashibara Biochemical Laboratories Co Ltd filed Critical Hayashibara Seibutsu Kagaku Kenkyujo KK
Publication of EP1321148A1 publication Critical patent/EP1321148A1/fr
Application granted granted Critical
Publication of EP1321148B1 publication Critical patent/EP1321148B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/702Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/16Emollients or protectives, e.g. against radiation
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52Stabilizers
    • A61K2800/522Antioxidants; Radical scavengers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/02Preparations for care of the skin for chemically bleaching or whitening the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations

Definitions

  • the present invention relates to an agent which inhibits reduction of active oxygen eliminating activity, uses of the same, and a method for inhibiting reduction of active oxygen eliminating activity. More particularly, the present invention relates to an agent for inhibiting reduction of active oxygen eliminating activity which comprises cyclo ⁇ 6 ⁇ - ⁇ -D-glucopyranosyl-(1 ⁇ 3)- ⁇ -D-glucopyranosyl-(1 ⁇ 6)- ⁇ -D-glucopyranosyl-(1 ⁇ 3)- ⁇ -D-glucopyranosyl-(1 ⁇ ), hereinafter abbreviated as "cyclotetrasaccharide", represented by Chemical Formula 1 as an effective ingredient, a method for inhibiting the reduction of plant active oxygen eliminating activity characterized in that it comprises the steps of incorporating either cyclotetrasaccharide or the inhibitory agent in the presence of an aqueous medium, and a composition which comprises a plant edible substance and/or a plant antioxidant where the reduction of active oxygen eliminating activity has been
  • these incurable diseases may relate to active oxygen molecules such as superoxide which is an oxygen molecule having an unpaired electron and relatively high reactivity, and derivatives thereof including hydroxyradical and hydrogen peroxide. It is believed that these molecules oxidize intracellular target molecules such as membrane lipids, proteins, and DNAs to induce oxygen-related defects and cause aging of living bodies and related diseases thereof.
  • active oxygen molecules such as superoxide which is an oxygen molecule having an unpaired electron and relatively high reactivity, and derivatives thereof including hydroxyradical and hydrogen peroxide. It is believed that these molecules oxidize intracellular target molecules such as membrane lipids, proteins, and DNAs to induce oxygen-related defects and cause aging of living bodies and related diseases thereof.
  • Enzymes capable of eliminating active oxygen such as superoxide dismutase (EC 1.15.1.1) and catalase (EC 1.11.1.6), and antioxidants such as L-ascorbic acid and ⁇ -tocopherol exist in living cells, so that the concentration of intracellular active oxygen is generally kept at a remarkably low level.
  • irradiation from a relatively-large amount of ultraviolet rays, radiations, and magnetic waves, excessive physical exercise, great mental stress, and aging form active oxygen in an amount that cannot be eliminated by the active oxygen eliminating activity of living bodies. This results in an accumulation of compounds oxidized by the excessive amount of active oxygen which causes the aforesaid oxygen-related defects.
  • Japanese Patent Kokai Nos To improve the problem, for example, Japanese Patent Kokai Nos.
  • the objects of the present invention is to provide a novel reduction inhibitory agent for active oxygen eliminating activity, a novel method for inhibiting the reduction of active oxygen eliminating activity, and a composition which comprises plant edible substances and/or plant antioxidants where the reduction of active oxygen eliminating activity is inhibited by the above method.
  • the first object of the present invention is to provide a reduction inhibitory agent for active oxygen eliminating activity which comprises cyclotetrasaccharide as an effective ingredient.
  • the second object of the present invention is to provide a method for inhibiting the reduction of plant active oxygen eliminating activity which is characterized in that it comprises a step of incorporating either cyclotetrasaccharide or the inhibitory agent into plant substances with active oxygen eliminating activity.
  • the third object of the present invention is to provide a composition that the reduction of active oxygen eliminating activity is inhibited by the above method.
  • the present inventors studied the use of saccharides and continued studying. They examined influence of saccharides on the reduction inhibitory effect for active oxygen eliminating activity of plant substances such as edible plant substances and plant antioxidants by incorporating saccharides therein. As a result, the present inventors found that cyclotetrasaccharide represented by Chemical Formula 1 exerts a more effective activity than other saccharides and strongly inhibits the reduction of plant active oxygen eliminating activity, and thus accomplished the present invention.
  • a cyclotetrasaccharide represented by Chemical Formula 1 is a non-reducing saccharide having a cyclic structure of cyclo ⁇ 6 ⁇ - ⁇ -D-glucopyranosyl-(1 ⁇ 3)- ⁇ -D-glucopyranosyl-(1 ⁇ 6)- ⁇ -D-glucopyranosyl-(1 ⁇ 3)- ⁇ -D-glucopyranosyl-(1 ⁇ ) composed of glucose molecules via the ⁇ -1,3 and ⁇ -1,6 bonds as disclosed in Carbohydrate Research, Vol. 329, pp. 655-665, 2000, by Gail M. Bradbrook.
  • the saccharide can be obtained from starch by an enzyme saccharifying method which utilizes ⁇ -isomaltosylglucosaccharide-forming enzyme and ⁇ -isomaltosyl-transferring enzyme in accordance with the methods as disclosed in International Patent Application Nos. PCT/JP01/04276 and PCT/JP01/06412 by the same applicant as the present invention.
  • Any form of cyclotetrasaccharide such as a syrup, crystalline powder of massecuite, crystalline hydrate, crystalline anhydride, or amorphous solid can be arbitrarily used.
  • the cyclotetrasaccharide content in the present reduction inhibitory agent for active oxygen eliminating activity can be selected from those which exert a desired reduction inhibitory activity on the active oxygen eliminating activity of edible plant substance, usually, at least about 10 % (w/w) (in the present specification, "%” means % (w/w) unless specified otherwise) on a dry solid basis (d.s.b.), preferably at least about 20 %, d.s.b., and more preferably at least about 50 %, d.s.b.
  • Cyclotetrasaccharide can be preferably incorporated into compositions containing edible plant substances and/or plant antioxidants in an amount of at least about one percent, preferably at least about five percents, and more preferably at least about 20 %, d.s.b.
  • the reduction inhibitory activity for active oxygen eliminating activity may be rather insufficient.
  • the term "on a dry solid basis (d.s.b.)" in the present invention means "under an ideal dried condition with no moisture, the weight of the composition comprising edible plant substances and/or plant antioxidants of the present invention".
  • d.s.b. can be calculated by substantially measuring a water weight of a composition, which cannot be removed in a conventional drying step, in a method such as the Karl-Fischer's method and subtracting the measured water weight from the dried weight of the composition.
  • incorporating in the present invention means "coexisting".
  • any conventional methods can be used as long as the agent exerts a reduction inhibitory activity for plant active oxygen eliminating activity.
  • the present agent can be preferably incorporated into plant edible substances and/or plant antioxidants by allowing cyclotetrasaccharide to contact with the substances and/or the antioxidants in the presence of an aqueous medium as homogeneously as possible.
  • the aqueous medium is usually water, and occasionally an aqueous solution comprising materials such as acids, bases, minerals, saccharides, alcohols, amino acids, and proteins, for example, sea water, ocean deep water, milk, serum, and soup, in an amount which does not affect the effect of the present invention.
  • cyclotetrasaccharide can be incorporated into the edible plant substances either by sprinkling cyclotetrasaccharide in a solid form over the substances and mixing them to melt and incorporate cyclotetrasaccharide into the substances, or by soaking the edible plant substances in cyclotetrasaccharide in a syrup form to incorporate cyclotetrasaccharide into the plant organs as homogeneously as possible.
  • Conditions such as temperatures and times in incorporating cyclotetrasaccharide by contacting it with edible plant substances can be appropriately selected, if necessarily.
  • the plant substances with active oxygen eliminating activity which can be used in the present invention mean edible plants per se; disrupted, minced, pulverized, dried, pickled, and extracted products of edible parts of the edible plants; and/or plant antioxidants.
  • Examples of the edible plants arbitrarily used in the present invention are edible root crops such as carrots, lotus roots, onions, burdocks, Japanese radishes, taros, yams, sweet potatoes, and potatoes; leafy vegetables such as lettuces, chicories, Chinese cabbages, cabbages, kales, moreheiya or Corchorus olitorius, Angelica keiskei, spinach, Malabar nightshades, Brassica campestris, Brassica rapa, Chrysanthemum aoronirium, ging-geng-cai or pak-choi, and turnips; fruiting vegetables such as gumbos, cauliflowers, broccolis, eggplants, tomatoes, cucumbers, pumpkins, zucchini, green peppers, field peas, and kidney beans;
  • plant antioxidants can be arbitrarily selected and used as the present plant antioxidants: plant enzymes having an active oxygen eliminating activity such as superoxide dismutase, catalase, and peroxidase; plant pigments such as rutin, ⁇ -glucosyl rutin, hesperidin, ⁇ -glucosyl hesperidin, naringin, ⁇ -glucosyl naringin, chlorophyll, carotenoid, and anthocyanin; plant polyphenols such as gallic acid, catechin, ⁇ -glucosyl catechin, tannic acid, enzogenol (pine coat extracts), and grape seed extracts; and plant vitamins such as ⁇ -tocopherol, L-ascorbic acid, and riboflavin.
  • plant enzymes having an active oxygen eliminating activity such as superoxide dismutase, catalase, and peroxidase
  • plant pigments such as rutin, ⁇ -glucosyl rutin, hes
  • compositions thus obtained are usually syrupy, pasty, or juicy disrupted products which have a relatively-high moisture content and require a relatively-low storage-temperature for a stable shelf life.
  • the compositions can be directly dried and/or pulverized, or dried and/or pulverized after sterilization by heating to obtain powdery or small pieces of solid compositions. Conventional drying and pulverizing methods can be arbitrarily used in the present invention.
  • the compositions can be prepared into powdery products by:
  • the powdery products can be arbitrarily granulated, tabletted, and encapsulated into appropriate forms for use.
  • the solid compositions in a relatively-highly processed will acquire more improved activity for inhibiting the reduction of active oxygen eliminating activity, storage stability, and handelability.
  • the solid compositions containing edible plant substances have features such that they effectively inhibit the deterioration of plant pigments contained in the edible plants as a material such as chlorophylls, carotenoids, anthocyanins, and flavonoids. Additionally, they satisfactorily retain the inherent color of pigments and mask undesirable tastes such as bitterness and astringency.
  • compositions according to the present invention containing cyclotetrasaccharide and an edible plant substance or plant antioxidant, which inhibit the reduction of active oxygen eliminating activity can be further mixed with one or more appropriate substances in a solid or liquid form such as essential minerals, edible fibers, saccharides for promoting the growth of bifid bacteria, vitamins, biologically active substances, and preservatives.
  • saccharides As the saccharides, trehalose, maltitol, and mannitol can be used. Essential minerals such as calcium, magnesium, phosphorus, iron, copper, zinc, and cobalt can be used in an appropriate amount.
  • pectin As the edible fibers, pectin, alginic acid, carrageenan, gum Arabic, glucomannan, cyclodextrin, and pullulan can be used. Particularly, trehalose and/or pullulan and/or cyclodextrin are preferable and can be advantageously used with cyclotetrasaccharide to produce the compositions according to the present invention.
  • saccharides which can be used to promote the growth of bifid bacteria, are lactosucrose, fructooligosaccharide, galactooligosaccharide, and isomaltooligosaccharide; and which can be arbitrarily used, if necessarily.
  • the vitamins advantageously used in the present invention include, for example, water soluble vitamins such as thiamin, riboflavin, L-ascorbic acid, rutin, hesperidin, naringin, niacin, pyridoxine, cyanocobalamin, and derivatives thereof; and lipid-soluble vitamins such as vitamin A, vitamin D, ⁇ -tocopherol, vitamin K, and derivatives thereof.
  • One or more biologically active substances such as hormones, antibiotics, cytokines, and propolis can be used, if necessarily.
  • Adequate amounts of ethanol, acetic acid, lactic acid, and salt can be used as preservatives, if necessarily.
  • compositions of the present invention To improve the quality of the compositions of the present invention and products containing the compositions, adequate flavoring agents, coloring agents, taste-imparting agents, stabilizers, and excipients can be advantageously used.
  • the reduction inhibitory agent for active oxygen eliminating activity with cyclotetrasaccharide as an effective ingredient according to the present invention can be advantageously incorporated into plant substances with active oxygen eliminating activity to inhibit the reduction of active oxygen eliminating activity.
  • the cyclotetrasaccharide content in the reduction inhibitory agent for active oxygen eliminating activity can be selected from those which exert a reduction inhibitory activity on the active oxygen eliminating activity of edible plant substances, usually, at least about 10 %, d.s.b., preferably, at least 20 %, d.s.b., and more preferably, at least 50 %, d.s.b.
  • the present reduction inhibitory agent can be consisted of cyclotetrasaccharide as an effective ingredient and prepared with one or more other substances selected from the aforesaid essential minerals, fibers, saccharides for promoting the growth of bifid bacteria, vitamins, biological active substances, and preservatives, if necessarily.
  • the reduction inhibitory agent for active oxygen eliminating activity may be in any forms such as a syrup, powder, granule, or tablet. Any methods can be used in the present reduction inhibitory agent as long as the agent exerts a reduction inhibitory activity for plant active oxygen eliminating activity.
  • the reduction inhibitory agent for active oxygen eliminating activity can be used according to the aforesaid method, which is incorporated cyclotetrasaccharide into plant substances with active oxygen eliminating activity, to inhibit the reduction of the activity.
  • the reduction inhibitory effect for plant active oxygen eliminating activity can be advantageously exerted to easily produce compositions which the reduction of the activity is inhibited.
  • compositions of the present invention can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and inhibit carcinogenesis.
  • the compositions can be used in food products, cosmetics, pharmaceuticals, and components and processing intermediates thereof.
  • compositions of the present invention can be used for health food products and other food products in general.
  • seasonings such as "furikake” (a seasoned fish meal), sauces, ketchup, “yakiniku-no-tare " (a sauce for Japanese grilled meat), curry roux, and instant soup mixes; Japanese and Western cakes such as “mochi” (a rice paste), “dango” (a ball of rice paste), candies, chewing gum, baked confections, snack confections, waffles, sponge cakes, buns, and breads; frozen desserts such as ice cream and ice candies; pastes such as fruit pastes, fruit sources, peanut pastes, and raw jams; pickles and pickled products; meat products such as hams and sausages; products of fish meats such as "kamaboko” (a steamed fish paste), “chikuwa” (a kind of fish paste), “hanpen” (a fish cake), and sausages; "chinmi” (a de
  • compositions according to the present invention can be used in cosmetics such as skin-beautifying agents, packs, creams, shampoos, hair rinses, hair tonics, bath salts, enzymic agents, and tooth pastes in the form of a liquid, paste, powder, or granule; and used as a component of a processing intermediate for these products.
  • compositions according to the present invention can be used in pharmaceuticals such as an oral and/or intubation nutrient, curative, and interferon-inducing agent in the form of a liquid, paste, granule, tablet, or capsule. Additionally, they can be used to treat and prevent aging-related diseases in the form of an oral and/or intubation nutrient or therapeutic agent such as a coilunarium, nebula, digestive agent, stomachic, enzymic agent, ointment, cataplasm, and their components and processing intermediates.
  • an oral and/or intubation nutrient or therapeutic agent such as a coilunarium, nebula, digestive agent, stomachic, enzymic agent, ointment, cataplasm, and their components and processing intermediates.
  • compositions of the present invention comprises food materials and can be used with less fear of causing toxicity.
  • the compositions can be usually administered to subjects; on a dry solid basis at a dose of about 0.1 to 1,000 g/adult/day, preferably, about 0.2 to 500 g/adult/day, and more preferably, about 1 to 100 g/adult/day; and administered to subjects intubationally, percutaneously, and permucosally similarly as in the oral administration.
  • the supernatant was collected by centrifugation the culture at 10,000 rpm for 30 min.
  • the resulting supernatant had about 0.45 unit/ml of the ⁇ -isomaltosylglucosaccharide-forming enzyme, i.e., a total enzymatic activity of about 8,110 units; and about 1.5 units/ml of ⁇ -isomaitosyl-transferring enzyme, i.e., a total enzymatic activity of about 26,900 units.
  • This supernatant was salted out with 80 % saturated ammonium sulfate and allowed to stand at 4 °C for 24 hours, and the formed sediments were collected by centrifugation at 10,000 rpm for 30 min, dissolved in 10 mM phosphate buffer (pH 7.5), and dialyzed against a fresh preparation of the same buffer to obtain about 400 ml of a crude enzyme solution with 8,110 units of the ⁇ -isomaltosylglucosaccharide-forming enzyme, 24,700 units of ⁇ -isomaltosyl-transferring enzyme, and about 15,600 units of cyclotetrasaccharide-forming activity.
  • the activities of these enzymes were assayed as follows: The ⁇ -isomaltosylglucosaccharide-forming enzyme was assayed for enzymatic activity by dissolving maltotriose in 100 mM acetate buffer (pH 6.0) to give a concentration of two percents (w/v) for a substrate solution, adding a 0.5 ml of an enzyme solution to a 0.5 ml of the substrate solution, enzymatically reacting the mixture solution at 35 °C for 60 min, stopping the reaction by boiling for 10 min, and quantifying maltose among the isomaltosyl maltose and maltose formed in the reaction mixture on high-performance liquid chromatography (abbreviated as "HPLC" hereinafter).
  • HPLC high-performance liquid chromatography
  • HPLC was carried out using "YMC Pack ODS-AQ303 column", a silica column commercialized by YMC Co., Ltd., Kyoto, Japan, at a column temperature of 40 °C and a flow rate of 0.5 ml/min of water, and using "RI-8012", a differential refractometer commercialized by Tosoh Corporation, Tokyo, Japan.
  • RI-8012 a differential refractometer commercialized by Tosoh Corporation, Tokyo, Japan.
  • One unit activity of the ⁇ -isomaltosylglucosaccharide-forming enzyme is defined as the enzyme amount that forms one micromole of maltose per minute under the above enzymatic reaction conditions.
  • the ⁇ -isomaltosyl-transferring enzyme was assayed for enzymatic activity by dissolving panose in 100 mM acetate buffer (pH 6.0) to give a concentration of two percents (w/v) for a substrate solution, adding a 0.5 ml of an enzyme solution to 0.5 ml of the substrate solution, enzymatically reacting the mixture solution at 35 °C for 30 min, stopping the reaction by boiling for 10 min, and quantifying glucose among the cyclotetrasaccharide and glucose formed in the reaction mixture by the glucose oxidase method.
  • One unit activity of the ⁇ -isomaltosyl-transferring enzyme is defined as the enzyme amount that forms one micromole of glucose per minute under the above enzymatic reaction conditions.
  • the cyclotetrasaccharide-forming activity is assayed by dissolving "PINE-DEX #100TM", a partial starch hydrolysate commercialized by Matsutani Chemical Ind., Tokyo, Japan, in 50 mM acetate buffer (pH 6.0) to give a concentration of two percents (w/v) for a substrate solution, adding 0.5 ml of an enzyme solution to 0.5 ml of the substrate solution, enzymatically reacting the mixture solution at 35 °C for 60 min, stopping the reaction by boiling at 100 °C for 10 min, and then further adding to the resulting mixture one milliliter of 50 mM acetate buffer (pH 5.0) with 70 units/ml of "TRANSGLUCOSIDASE L AMANOTM", an ⁇ -glucosidase commercialized by Amano Pharmaceutical Co., Ltd., Aichi, Japan, and 27 units/ml of a glucoamylase commercialized by Nagase Biochemicals , Ltd.
  • the reaction mixture was heated at 100 °C for 10 min to inactivate the remaining enzymes and a portion of the reaction mixture was sampled and then quantified on HPLC for the formation yield of cyclotetrasaccharide, revealing that it contained about 84 % cyclotetrasaccharide on a saccharide composition basis.
  • HPLC was carried out by using "SHODEX KS-801 column", commercialized by Showa Denko K. K., Tokyo, Japan, at a column temperature of 60 °C and a flow rate of 0.5 ml/min of water, and using "RI-8012", a differential refractometer commercialized by Tosoh Corporation, Tokyo, Japan.
  • the reaction mixture was adjusted to pH 5.0 and 45 °C , and then incubated for 24 hours after admixed with 1,500 units/ g starch of "TRANSGLUCOSIDASE AMANOTM", an ⁇ -glucosidase commercialized by Amano Pharmaceutical Co. , Ltd., Aichi, Japan, and 75 units/g starch of "XL-4TM", a glucoamylase commercialized by Nagase Biochemicals, Ltd., Kyoto, Japan, to decompose the remaining reducing oligosaccharides.
  • the resulting culture was adjusted to pH 5.8 by the addition of sodium hydroxide and incubated at 90 °C for one hour to inactivate the remaining enzymes and filtered to remove insoluble substances.
  • the filtrate was concentrated using "HOLLOSEP HR5155PITM", a reverse osmosis membrane by Toyobo Co. , Ltd., Osaka, Japan, to give a concentration of about 16 %, d.s.b., and the concentrate was in a conventional manner decolored, desalted, filtered, and concentrated to obtain about 6.2 kg of an aqueous saccharide solution with a solid content of about 3,700 g.
  • the aqueous saccharide solution was fed to a column packed with about 225 L of "AMBERLITE CR-1310 (Na + -form)TM", an ion-exchange resin commercialized by Japan Organo Co., Ltd., Tokyo, Japan, and chromatographed at a column temperature of 60 °C and a flow rate about 45 L/h. While the saccharide composition of elute from the column was monitored by the aforesaid HPLC, fractions with a purity of at least 98 % of cyclotetrasaccharide were collected, and in a conventional manner desalted, decolored, filtered, and concentrated to obtain about 7.5 kg of an aqueous saccharide solution with a solid content of about 2,500 g.
  • ABERLITE CR-1310 Na + -form
  • ion-exchange resin commercialized by Japan Organo Co., Ltd., Tokyo, Japan
  • HPLC measurement for saccharide composition of the aqueous saccharide solution revealed that it contained cyclotetrasaccharide with a purity of about 99.5%.
  • the obtained aqueous saccharide solution containing cyclotetrasaccharide was concentrated by evaporation to give a concentration of about 50 %, d.s.b.
  • About five kilograms of the concentrate was placed in a cylindrical plastic vessel and then crystallized by lowering the temperature of the concentrate from 65 °C to 20 °C for about 20 hours under gentle rotatory conditions.
  • the crystallized concentrate was separated by a centrifugal filter to obtain 1,360 g by wet weight of a crystal of cyclotetrasaccharide.
  • Fresh raw carrots were disrupted by a mixer, and saccharides were respectively added to the mixture and dissolved therein to give a concentration of 10 %, d.s.b.
  • the solutions were dried under a reduced pressure at 40 °C for two days, dried in vacuo at the same temperature for 24 hours, and pulverized by a mixer into powdery carrot compositions.
  • the saccharides used were the cyclotetrasaccharide obtained in Experiment 2 and commercialized reagent-grade glucose, mannitol, sorbitol, maltose, sucrose, trehalose, and pullulan.
  • compositions An about 100 g each of the compositions was placed and sealed in a 500-ml polystyrene container, and stored at 40 °C for seven days.
  • the active oxygen eliminating activities of the compositions before and after storage were compared with each other.
  • the active oxygen eliminating activity was assayed by the nitroblue tetrazolium (NBT) test by Toshio IMANARI et al. in Igakuno Ayumi, Vol. 101, pp. 496-497 (1977), and the level of superoxide, formed in a xanthine-xanthine oxidase system, was assayed by quantifying calorimetrically the content of formazan formed by reducing NBT.
  • refined water was used as a test solution.
  • One unit activity of active oxygen eliminating activity was defined as that inhibited 50 % formazan formation as compared with the control.
  • Table 1 shows the composition of the powdery compositions and the active oxygen eliminating activity per gram of the compositions before and after storage. As evident from Table 1, among the saccharides tested the composition with cyclotetrasaccharide or trehalose showed the highest residual percentage for active oxygen eliminating activity, revealing that cyclotetrasaccharide exerts a remarkable effect on the reduction inhibitory activity for active oxygen eliminating activity similar to trehalose. Thus cyclotetrasaccharide is preferable as an effective ingredient for a reduction inhibitory agent for active oxygen eliminating activity. Next to cyclotetrasaccharide and trehalose, pullulan showed a relatively-high reduction inhibitory activity for active oxygen eliminating activity.
  • Fresh raw carrots were disrupted as Experiment 3, and saccharides were respectively added to the mixture and dissolved therein to give a concentration of 10 %, d.s.b.
  • the solutions were dried under a reduced pressure at 40 °C for one day, dried in vacuo at the same temperature for 17 hours, and pulverized by a mixer into powdery carrot compositions.
  • the saccharides used were the cyclotetrasaccharide obtained in Experiment 2 and commercialized reagent-grade glucose, maltose, and trehalose. About 100 g each of the compositions was placed and sealed in a 500-ml polystyrene container, and stored at 40°C for seven or fourteen days.
  • the activity of active oxygen eliminating activity was defined with reference to the standard.
  • Table 2 shows the compositions of the powdery compositions and the active oxygen eliminating activity per gram each of the compositions before and after storage.
  • the composition with cyclotetrasaccharide or trehalose showed the highest residual percentage for active oxygen eliminating activity, revealing that cyclotetrasaccharide exerted a remarkable effect on the reduction inhibitory activity for active oxygen eliminating activity similar to trehalose.
  • cyclotetrasaccharide is preferable as an effective ingredient for a reduction inhibitory agent for active oxygen eliminating activity.
  • Table 3 shows that at least about one percent, preferably, at least about five percents, and more preferably, at least about 20 % of cyclotetrasaccharide, d.s.b., exerted a desired effective reducing inhibitory activity for active oxygen eliminating activity.
  • Vegetables were treated similarly as in Experiment 3, and cyclotetrasaccharide was respectively added to the disrupted vegetables to give a concentration of 10 %, d.s.b.
  • the resulting mixtures were dried in vacuo at 45 °C for 20 hours, and pulverized into powdery vegetable compositions.
  • each composition was respectively placed in a container and stored at 40 °C for six days.
  • the active oxygen eliminating activity of one gram each of the compositions before and after storage was compared with that of the composition prepared without cyclotetrasaccharide.
  • Table 4 shows the compositions of the powdery compositions and their active oxygen eliminating activities.
  • a reduction inhibitory activity for active oxygen eliminating activity by incorporating cyclotetrasaccharide was observed in many vegetables such as carrot, onion, Japanese radish, cabbage, spinach, cucumber, and pumpkin.
  • cyclotetrasaccharide solution which is prepared by using cyclotetrasaccharide obtained in Experiment 2, was dissolved five micrograms ( ⁇ g) of superoxide dismutase from a horseradish commercialized by Sigma Chemical Co., St.
  • cyclotetrasaccharide exerts an effective reducing inhibitory activity for active oxygen eliminating activity of plant antioxidants such as superoxide dismutase, ⁇ -glucosyl hesperidin, ⁇ -glucosyl rutin, gallic acid, and catechin.
  • plant antioxidants such as superoxide dismutase, ⁇ -glucosyl hesperidin, ⁇ -glucosyl rutin, gallic acid, and catechin.
  • a reducing inhibitory agent for active oxygen eliminating activity which comprises cyclotetrasaccharide as an effective ingredient, could scarcely exert the desired activity only when mixed in a powdery form with powdery substances having active oxygen eliminating activity, but exert the desired activity when cyclotetrasaccharide in a melted state is allowed to contact with and incorporate into the substances, or when cyclotetrasaccharide is incorporated into the substances in an aqueous system.
  • Corn starch was prepared into an about 20 % starch suspension which was mixed with 0.1 % calcium carbonate, adjusted to pH 6.5, mixed with 0.3 % per gram starch of "TERMAMYL 60LTM", an ⁇ -amylase commercialized by Novo Industri A/S, Copenhagen, Denmark, reacted at 95 °C for 15 min, autoclaved at 120 °C for 20 min, and promptly cooled to about 35 °C to obtain a liquefied solution with DE of about four.
  • the liquefied solution was admixed with 0.2 ml per gram starch of an enzyme solution containing ⁇ -isomaltosylglucosaccharide-forming enzyme and ⁇ -isomaltosyl-transferring enzyme from Bacillus globisporus C9 strain obtained by the method in Experiment 1, and 10 units per gram solid starch of cyclomaltodextrin glucanotransferase commercialized by Hayashibara Biochemical Laboratories, Inc., Okayama Japan, adjusted to pH 6.0, and reacted at 35 °C for 48 hours.
  • reaction mixture was incubated at 95 °C for 30 min, it was adjusted to pH 5.0 and 50 °C , and then admixed with 300 unites per gram solid substance of "TRANSGLUCOSIDASE L AMANOTM", an ⁇ -glucosidase commercialized by Amano Pharmaceutical Co., Ltd., Aichi, Japan, and reacted for 24 hours.
  • the reaction mixture was admixed with 30 units per gram solid substance of "GLUCOZYMETM, a glucoamylase, commercialized by Nagase Biochemicals, Ltd., Kyoto, Japan, reacted for 17 hours, incubated at 95 °C for 30 min, cooled down, and filtrated.
  • the obtained filtrate was in a conventional manner decolored by using an activated carbon, desalted by using H- and OH-types ion-exchanging resins, purified, and concentrated to obtain a cyclotetrasaccharide content syrup with the concentration of 60 % which contains 34.2 % of glucose, 62.7 % of cyclotetrasaccharide, and 3.1 % of other saccharides, d.s.b.
  • the cyclotetrasaccharide content syrup was fractionated by using "AMBERLITE CR-1310 (Na + -form)TM", a strong acidic cation-exchange resin commercialized by Japan Organo Co., Ltd., Tokyo, Japan.
  • the resin was packed in four stainless steal jacketed-columns, 5.4 cm in diameter and five meters in length. The columns were connected in series to a total resin length of 20 m. While the column temperature was kept at 60 °C, the cyclotetrasaccharide content syrup was fed to the columns at a ratio of five percents (v/v) resin and fractionated by feeding a warm water of 60 °C at SV (space velocity) 0.13.
  • the cyclotetrasaccharide high content solution was concentrated to the concentration of about 70 %, and then placed in a crystallizer, admixed with about two percents of a seed crystal of crystalline cyclotetrasaccharide hydrate, and cooled to obtain a massecuite with a crystallization degree of about 45 %.
  • the massecuite was sprayed from a nozzle on a dried tower at relatively-high pressure of 150 kg/cm 2 .
  • the powdery saccharide is a high-purity crystalline cyclotetrasaccharide hydrate, and it is preferable as a reduction inhibitory agent for active oxygen eliminating activity and can be arbitrarily used to inhibit the reduction of active oxygen eliminating activity of plant edible substances.
  • the product can be arbitrarily used in a reduction inhibitory agent for active oxygen eliminating activity of plant edible substances.
  • a cyclotetrasaccharide content syrup with the concentration of 60 %, obtained by the method in Example A-1 was dissolved by homogeneously mixing to 0.5 parts by weight of pullulan, and 0.5 parts by weight of a readily-water-soluble cyclodextrin into a syrupy reduction inhibitory agent for active oxygen eliminating activity.
  • the product can be arbitrarily used in a reduction inhibitory agent for active oxygen eliminating activity of plant edible substances.
  • Example A-1 In one hundred parts by weight of a high-purity crystalline cyclotetrasaccharide hydrate, obtained by the method in Example A-1, was dissolved by homogeneously mixing 100 parts by weight of crystalline trehalose hydrate, one part by weight of pullulan, and one part by weight of a readily-water-soluble cyclodextrin into a powdery reduction inhibitory agent for active oxygen eliminating activity.
  • the product can be arbitrarily used in a reduction inhibitory agent for active oxygen eliminating activity of plant edible substances.
  • Fresh spinach was disrupted by a mixer, and in 10 parts by weight of the resulting disruptant were mixed by dissolving one part by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-4 and 0.1 part by weight of ⁇ -glucosyl rutin in an appropriate volume of water.
  • the resulting mixture was heated at 100°C for 10 min, dried with air heated to 40°C for two hours, dried in vacuo at 40°C for 16 hours, and powdered by a pulverizer to obtain a composition containing spinach having an active oxygen eliminating activity of about 1,200 units per gram composition.
  • the composition satisfactorily retained the inherent color of spinach and stimulated the appetite.
  • Intake of the composition enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers inherent to the spinach, and imparts the active oxygen eliminating activity to the living bodies.
  • the composition can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be arbitrarily used as a food product, cosmetic, pharmaceutical, or their material or processing intermediates.
  • Cabbage was cut, branched, and sliced by a cutter into fine strips with about five millimeters in width. Ten parts by weight of the fine strips was mixed with one part by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-3, and 0.05 part by weight of ⁇ -glucosyl rutin, and the mixture was allowed to stand at ambient temperature for two hours, then dried by air heated to 40 °C for two hours, dried in vacuo at 40 °C for 16 hours to obtain a composition containing fine strips of cabbage having an active oxygen eliminating activity of about 1,300 units per gram composition. The composition retained satisfactorily the inherent color of cabbage and stimulated your appetite.
  • Intake of the composition enriches living bodies with functional ingredients such as vitamins, and edible fibers inherent to the cabbage, and imparts the active oxygen eliminating activity to the living bodies.
  • the composition can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be arbitrarily used as a food product, cosmetic, pharmaceutical, or their material or processing intermediates.
  • a fresh eggplant was sliced, and the sliced eggplant was washed with water.
  • One part by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-1, was dissolved in an appropriate volume of water and mixed with 10 parts by weight of the sliced eggplant, and the resulting mixture was dried by air heated to 70 °C for two days to obtain a composition containing sliced eggplant having an active oxygen eliminating activity of about 11,000 units per gram composition.
  • the composition retained the inherent color of eggplant's skin and stimulated the appetite. Intake of the composition enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers inherent to the eggplant, and imparts the active oxygen eliminating activity to the living bodies.
  • the composition can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be arbitrarily used as a food product, cosmetic, pharmaceutical, or their material or processing intermediates.
  • a fresh carrot was branched and sliced by a slicer.
  • One part by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-4, was dissolved in an appropriate volume of water and mixed with 10 parts by weight of the sliced carrot.
  • the mixture was dried with air heated to 50 °C for 16 hours to obtain a composition containing sliced carrots having an active oxygen eliminating activity of about 450 units per gram composition.
  • the composition satisfactorily retained the color inherent to carrot, stimulated the appetite, and had a relatively-low hygroscopicity and a satisfactory shelf-life.
  • Intake of the composition enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers inherent to carrot, and imparts the active oxygen eliminating activity to the living bodies.
  • the composition can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be arbitrarily used as a food product, cosmetic, pharmaceutical, or their material or processing intermediates.
  • Dried Hizikia fusiforme was rehydrated in water and disrupted with a cutter.
  • 10 parts by weight of the disrupted mixture was dissolved by mixing five parts by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-2.
  • the solution was dried by air heated to 50 °C for eight hours, dried in vacuo at 40 °C, and pulverized into a composition containing Hizikia fusiforme having an active oxygen eliminating activity of about 24 units per gram composition.
  • Intake of the composition enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers inherent to Hizikia fusiforme, and imparts the active oxygen eliminating activity to the living bodies.
  • the composition can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be arbitrarily used as a food product, cosmetic, pharmaceutical, or their material or processing intermediates.
  • a dried Chinese mushroom was rehydrated in water, heated at 100 °C for 15 min, and disrupted by a cutter.
  • 100 parts by weight of the disrupted mixture was dissolved by mixing 0.1 part by weight of a tea extract and 10 parts by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-3, and the resulting mixture was dried at 50 °C for eight hours, dries in vacuo at 40 °C, and pulverized to obtain a composition containing a powdery Chinese mushroom having an active oxygen eliminating activity of about 560 units per gram composition.
  • Intake of the composition enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers inherent to Chinese mushroom, and imparts the active oxygen eliminating activity to the living bodies.
  • the composition can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be arbitrarily used as a food product, cosmetic, pharmaceutical, or their material or processing intermediates.
  • Citron peel was disrupted by a cutter, and five parts by weight of the disrupted peel was dissolved in an appropriate volume of water and mixed with one part by weight of a reduction inhibitory agent for active oxygen eliminating activity, obtained by the method in Example A-1. After preliminary freezing, the resulting mixture was freeze-dried for three days, and disrupted to obtain a composition containing a powdery citron having an active oxygen eliminating activity of about 12 units per gram composition.
  • the composition retains satisfactorily the color and flavor inherent to citron. Intake of the composition enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers inherent to the citron, and imparts the active oxygen eliminating activity to living bodies.
  • the composition can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be arbitrarily used as a food product, cosmetic, pharmaceutical, or their material or processing intermediates.
  • composition Containing Aojiso (a Beefsteak Plant)
  • Aojiso leaves were branched and disrupted by a mixer.
  • One part by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-1 and 0.5 part by weight of ⁇ -glucosyl rutin were dissolved in an appropriate volume of water and mixed with five parts by weight of the disrupted mixture was dissolved by mixing, then mixed with 35 parts by weight of crystalline cyclotetrasaccharide anhydride as a desiccant.
  • the resulting mixture was allowed to stand at ambient temperature for one day and disrupted by a crusher to obtain a composition containing a powdery aojiso having an oxygen eliminating activity of about 230 units per gram composition.
  • the composition satisfactorily retained the color, flavor and taste inherent to aojiso, and stimulated the appetite. Intake of the composition enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers inherent to the aojiso, and imparts the active oxygen eliminating activity to living bodies.
  • the composition can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be arbitrarily used as a food product, cosmetic, pharmaceutical, or their material or processing intermediates.
  • mugwort was placed into boiling water with an adequate amount of salt to remove harshness, dehydrated softly and disrupted by a crusher.
  • One point three (1.3) parts by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-5 and 0.05 part by weight of ⁇ -glucosyl rutin were dissolved in an appropriate volume of water and mixed with five parts by weight of the disrupted mixture.
  • the resulting mixture was dried by air heated to 50 °C for four hours, dried in vacuo at 40 °C for 16 hours, and disrupted to obtain a composition containing a powdery mugwort having an active oxygen eliminating activity of about 780 units per gram composition.
  • the composition satisfactorily retained the color, flavor and taste inherent to mugwort, and stimulated the appetite. Intake of the composition enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers inherent to mugwort, and imparts the active oxygen eliminating activity to the living bodies.
  • the composition can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be arbitrarily used as a food product, cosmetic, pharmaceutical, or their material or processing intermediates.
  • a 0.5 part by weight of a dried dokudami was mixed with 10 parts by weight of water, and heated to boiling for 90 min. A supernatant of the infused solution was collected by a basket-type centrifuge and boiled down to obtain four parts by weight of about five percents solution. Two parts by weight of he concentrate was mixed with 0.5 part by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-3, and the resulting solution was spray-dried in a conventional manner to obtain a composition containing a powdery dokudami extract having an active oxygen eliminating activity of about 1,400 units per gram composition. The composition had a lesser unsatisfactory smell and taste inherent to dokudami and could be more easily swallowable than conventional ones.
  • Intake of the composition enriches living bodies with functional ingredients such as vitamins, minerals, an edible fibers inherent to the dokudami, and imparts the active oxygen eliminating activity to living bodies.
  • the composition can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be arbitrarily used as a food product, cosmetic, pharmaceutical, or their material or processing intermediates.
  • a fresh aloe was disrupted by a mixer.
  • One part by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-1 was dissolved in an appropriate volume of water and mixed with 10 parts by weight of the disrupted aloe and 0.1 part by weight of a tea extract.
  • the resulting mixture was dried by air, heated to 70 °C for two days, and disrupted by a crusher to obtain a composition containing a powdery aloe having an active oxygen eliminating activity of 5,800 units per gram composition.
  • the composition had a lesser astringency of the aloe and was more easily swallowable than conventional ones.
  • Intake of the composition enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers inherent to aloe, and imparts the active oxygen eliminating activity to living bodies.
  • the composition can be satisfactorily used to maintain and promote health, prevent aging and geriatric diseases, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be arbitrarily used as a food product, cosmetic, pharmaceutical, or their material or processing intermediates.
  • a Chinese cabbage preserved with seasonings was cut by a chopping machine.
  • One part by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-1 was dissolved in an appropriate volume of water and mixed with 10 parts by weight of the cut product, and the mixture was dried with air heated to 55 °C for 16 hours to obtain a composition containing small pieces of Chinese cabbage, preserved with seasonings, having an active oxygen eliminating activity of about 5,400 units per gram composition.
  • the product retained the color tint inherent to Chinese cabbage. When tasted, the satisfactory taste and flavor spread throughout the mouth and stimulated the appetite. Intake of this composition enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers inherent to Chinese cabbage, and augments the active oxygen eliminating activity to the living bodies.
  • compositions can be satisfactorily used to maintain and promote health, prevent aging and geriatric disease, promote the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be used as a food product, cosmetic, pharmaceutical, or a component of processing intermediate thereof.
  • the compositions can also be used as food products such as furikake, premix for onigiri (a rice ball), and soup for Chinese noodles, and as a health food, cosmetic, pharmaceutical, or components and intermediates thereof.
  • a pickled Brassica rapa was cut by a chopping machine.
  • One part by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method in Example A-1 was dissolved in an appropriate volume of water and mixed with 10 parts by weight of the cut product.
  • the mixture was dried in air, heated to 55 °C for 16 hours to obtain a composition containing small pieces of pickled Brassica rapa having an active oxygen eliminating activity of about 2600 units per gram composition.
  • the product retained the color tint inherent to picked Brassica rapa. When tasted, the satisfactory taste and flavor spread throughout the mouth and stimulated the appetite. Intake of this composition enriches living bodies with functional ingredients such as vitamins, minerals and edible fibers inherent to pickled Brassica rapa, and augments the active oxygen eliminating activity to the living bodies.
  • the composition can be used to maintain and promote health, prevent aging and geriatric diseases, promote treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be used as a food product, cosmetic, pharmaceutical, or components or processing
  • Korean pickled Chinese cabbage was cut by a chopping machine.
  • One part by weight of a reduction inhibitory agent for active oxygen eliminating activity obtained by the method of Example A-4 was dissolved in an appropriate volume of water and mixed with 10 parts by weight of the cut product.
  • the mixture was air dried and heated to 55 °C for 16 hours to produce a composition containing small pieces of pickled Chinese cabbage having an active oxygen eliminating activity of about 1600 units per gram composition.
  • the product retained the color tine of Korean pickled Chinese cabbage. When tasted, the satisfactory taste and flavor spread throughout the mouth and stimulated the appetite.
  • Intake of the composition enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers inherent to Korean picked Chinese cabbage, and augments the active oxygen eliminating activity to the living bodies.
  • the composition can be used to maintain and promote health, prevent aging and geriatric disease, promotes the treatment of incurable diseases, and prevent carcinogenesis.
  • the composition can be used as a food product, cosmetic, pharmaceutical, or components or processing intermediates thereof.
  • a gum base Three parts by weight of a gum base was heated to be softened, then mixed with three parts by weight of crystalline cyclotetrasaccharide hydrate, three parts by weight of crystalline trehalose hydrate, one part by weight of a composition containing aojiso obtained by the method of Example B-9, and 0.01 parts by weight of a tea extract.
  • the resulting mixture was admixed with adequate amounts of flavor and color, kneaded by a roll in a conventional manner, shaped, and packaged into a product having an active oxygen eliminating activity of about 120 units per gram product.
  • the product is a chewing gum with satisfactory texture, flavor, and taste.
  • the product containing cyclotetrasaccharide and trehalose as a saccharide is not easily utilized by dental caries inducing microorganisms, and it does not cause dental caries.
  • Example B-10 Ten parts by weight of glutinous rice starch was mixed with 12 parts by weight of water, and the mixture was gelatinized by heating, then mixed with 0.5 part by weight of a composition containing mugwort obtained by the method of Example B-10.
  • the mixture thus obtained was shaped and packaged in a conventional manner to produce a dango having an active oxygen eliminating activity of over 12 units per gram content.
  • the product is a mugwort - dango, i.e., a rice paste with mugwort, having the inherent color tint, flavor, and taste to mugwort, and a satisfactory mouth feeling.
  • a composition was prepared from the following ingredients: 20 parts by weight of crystalline ⁇ -maltose, 1.1 parts by weight of glycine, 0.18 part by weight of sodium glutamate, 1.2 parts by weight of salt, one part by weight of citric acid, 0.4 part by weight of calcium lactate, 0.3 part by weight of a composition containing spinach obtained by the method of Example B-1, 0.01 part by weight of thiamine, and 0.01 part by weight of riboflavin. Twenty four grams of the composition were injected into small laminated aluminum bags and heat sealed to obtain a nutritional product for intubtaion having an active oxygen eliminating activity of over 12 units per gram composition. One bag of the nutritional product is dissolved in about 300-500 ml of water, and the solution can be administered to subjects orally or through the subjects' nasal cavities, stomachs, or intestines as a parenteral liquid nutritional supplement.
  • Two parts by weight of polyoxyethylene glycol monostearate, five parts by weight of glyceryl monostearate of self-emulsifying, 2.8 parts by weight of a composition containing aloe obtained by the method in Example B-12, 0.2 part by weight of ⁇ -glucosyl rutin, one part by weight of liquid petrolatum, 10 parts by weight of glyceryl trioctanate, and an adequate amount of an antiseptic were dissolved by heating in a conventional manner.
  • the resulting solution was admixed with two parts by weight of L-lactic acid, five parts by weight of 1,3-butylene glycol, and 66 parts by weight of refined water, and the mixture was emulsified by a homogenizer and admixed with an adequate amount of a flavor under stirring to obtain a cosmetic cream having an active oxygen eliminating activity of about 46 units per gram product.
  • the product can be used as a therapeutic or preventive agent for sunburned skin, as a skin beautifying agent, a skin whitening agent, and an agent for inhibiting aging of skin including chloasmas, freckles, pigmentation, and wrinkles.
  • Bath salts having an active oxygen eliminating activity of about 220 units per gram product were prepared by mixing 26 parts by weight of refined water and adequate amounts of a coloring agent and flavoring agent with 21 parts by weight of sodium DL-lactate, eight parts by weight of sodium pyruvate, five parts by weight of a composition containing citron obtained by the method of Example B-7, one part by weight of ⁇ -glucosyl rutin, and 40 parts by weight of ethanol.
  • the product can be suitable used as a skin beautifying agent and skin whitening agent by diluting 100-10,000 fold in hot water in a bathtub. Similarly as above, the product can be used by diluting it in water for a face wash or beauty wash.
  • One part by weight of sodium acetate trihydrate and four parts by weight of calcium DL-lactate were mixed to homogeneity with 10 parts by weight of glycerin, and this mixture was added to a mixture consisting of 50 parts by weight of petrolatum, 10 parts by weight of vegetable wax, five parts by weight of lanolin, 14.5 parts by weight of sesame oil, six parts by weight of a composition containing dokudami obtained by the method of Example B-11, and 0.5 part by weight of peppermint oil.
  • the mixture thus obtained was homogeneously mixed into an ointment having an active oxygen eliminating activity of about 54 units per gram.
  • the product can be used as an antipyogenic agent, skin beautifying agent, skin whitening agent, and agent for promoting the treatment of skin traumas and burns.
  • the present invention provides a reduction inhibitory agent for active oxygen eliminating activity which comprises cyclotetrasaccharide as an effective ingredient, a method for inhibiting the reduction of active oxygen eliminating activity comprising incorporating either cyclotetrasaccharide or the reduction inhibitory agent into products to be treated, and a composition which contains plant edible substance and/or plant antioxidant in which the reduction of active oxygen eliminating activity is inhibited by the above method.
  • Intake of the present composition easily nutritionally supplies living bodies and enriches living bodies with functional ingredients such as vitamins, minerals, and edible fibers of plant edible substances. Therefore, the present composition contributes greatly to maintain and promote health, prevent aging and geriatric diseases promote the treatment of incurable diseases, and inhibit carcinogenesis.
  • the present invention provides a novel health resource as a fourth functional ingredient which can be used in processing and use of plant edible substances.
  • the present invention provides a great contribution to a wide variety of fields, particularly the fields of food products, cosmetics, and pharmaceuticals.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Dermatology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Birds (AREA)
  • Biotechnology (AREA)
  • Psychiatry (AREA)
  • Immunology (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Toxicology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
EP02257948A 2001-11-20 2002-11-19 Utilisation de cyclotetrasaccharides pour augmenter l'activité d'élimination de l'oxygène actif Expired - Lifetime EP1321148B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001355273 2001-11-20
JP2001355273A JP4397142B2 (ja) 2001-11-20 2001-11-20 活性酸素消去能低減抑制剤

Publications (2)

Publication Number Publication Date
EP1321148A1 true EP1321148A1 (fr) 2003-06-25
EP1321148B1 EP1321148B1 (fr) 2006-05-24

Family

ID=19166999

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02257948A Expired - Lifetime EP1321148B1 (fr) 2001-11-20 2002-11-19 Utilisation de cyclotetrasaccharides pour augmenter l'activité d'élimination de l'oxygène actif

Country Status (6)

Country Link
US (2) US20030108593A1 (fr)
EP (1) EP1321148B1 (fr)
JP (1) JP4397142B2 (fr)
KR (1) KR100943559B1 (fr)
DE (1) DE60211632T2 (fr)
TW (1) TWI256292B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004020552A1 (fr) * 2002-08-30 2004-03-11 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Inhibiteurs de reactions radicalaires, procede d'inhibition de reactions radicalaires et utilisation associee
EP1652527A1 (fr) * 2003-07-18 2006-05-03 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Accelerateur d'absorption minerale et utilisation associee
KR100943559B1 (ko) * 2001-11-20 2010-02-22 가부시끼가이샤 하야시바라 세이부쓰 가가꾸 겐꾸조 활성산소 소거능 저감 억제제
CN108617757A (zh) * 2018-03-27 2018-10-09 荔浦县万家兴果蔬专业合作社 一种葡萄的保鲜方法

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005027944A1 (fr) 2003-09-22 2005-03-31 Purecell Technologies Inc. Compositions orales et voie d'administration d'un extrait de thylakoide
US8941668B2 (en) 2004-06-25 2015-01-27 Nvidia Corporation Method and system for a scalable discrete graphics system
US8411093B2 (en) 2004-06-25 2013-04-02 Nvidia Corporation Method and system for stand alone graphics independent of computer system form factor
KR101356330B1 (ko) * 2004-12-24 2014-01-27 가부시끼가이샤 하야시바라 세이부쓰 가가꾸 겐꾸조 간기능 개선제
JP4766653B2 (ja) * 2005-01-28 2011-09-07 株式会社林原生物化学研究所 眼科用医薬組成物
KR100689715B1 (ko) * 2005-09-22 2007-03-08 양건태 김치제조방법 및 이를 위한 김치포장방법과 그 포장체
KR20100014799A (ko) * 2007-01-17 2010-02-11 엔베쎄 뉴트라쇠틱 비지니스 컨썰팅 과일 및 야채를 함유하는 항산화 음식조성물, 그 제조 방법 및 용도
JP4503087B2 (ja) 2008-08-19 2010-07-14 稔 菅野 糖度向上、糖成分調整および呈味調整に関する素材、方法および果実・野菜類
BRPI1008607B1 (pt) 2009-02-23 2017-04-18 Unilever Nv composição cosmética comestível para o tratamento da pele envelhecida, método cosmético para proporcionar benefícios para a pele, e, usos da referida composição.
ES2556985T3 (es) 2011-01-11 2016-01-21 Capsugel Belgium Nv Nuevas cápsulas duras que comprenden pululano
JP7136765B2 (ja) * 2017-03-24 2022-09-13 株式会社林原 オートファジー誘導剤とその用途
BR112019021396A2 (pt) 2017-04-14 2020-04-28 Capsugel Belgium Nv processo para fabricação de pululano
CA3059527A1 (fr) 2017-04-14 2018-10-18 Capsugel Belgium Nv Capsules de pullulane

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0868916A2 (fr) * 1997-03-04 1998-10-07 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Agent-inhibiteur de la réduction pour l'activité d'élimination d'oxygène actif
EP1229112A1 (fr) * 2000-08-01 2002-08-07 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Synthase d'alpha-isomaltosylglucosaccharide, procede de preparation et utilisation associes
EP1284286A1 (fr) * 2000-05-22 2003-02-19 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Alpha-isomaltosyltransferase, procede de production et utilisation

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5231019B2 (fr) * 1973-10-16 1977-08-12
US5969214A (en) * 1990-06-11 1999-10-19 Calgene, Inc. Glycogen biosynthetic enzymes in plants
JP2823706B2 (ja) * 1991-02-07 1998-11-11 三共株式会社 品質安定化剤
JP2933774B2 (ja) * 1991-12-19 1999-08-16 七郎 庭野 葉類加工食品及びその製法
JP3212706B2 (ja) * 1992-08-05 2001-09-25 日本食品化工株式会社 飲食物
JP3168550B2 (ja) * 1992-12-02 2001-05-21 株式会社林原生物化学研究所 脱水剤およびそれを用いる含水物の脱水方法並びにその方法で得られる脱水物品
JPH08143466A (ja) * 1994-11-15 1996-06-04 Sanki Shoji Kk 天然抗酸化剤および活性酸素消去剤
US5786196A (en) * 1995-06-12 1998-07-28 The United States Of America As Represented By The Secretary Of Agriculture Bacteria and enzymes for production of alternan fragments
DE69731016T2 (de) * 1996-03-04 2005-10-06 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Herstellung einer Trehalulose enthaltende Polysaccharidzusammensetzung.
JPH10279458A (ja) * 1997-04-01 1998-10-20 Nisshin Oil Mills Ltd:The 組成物
JP4295840B2 (ja) * 1997-12-09 2009-07-15 株式会社林原生物化学研究所 血行改善剤
JP3364442B2 (ja) * 1998-12-25 2003-01-08 日本食品化工株式会社 退色防止剤、活性酸素消去剤、飲食品の退色防止法及び飲食品の活性酸素消去能を増強させる方法
US6536181B1 (en) * 1999-01-13 2003-03-25 Won Kee Hong Composite retaining wall and construction method for underground structure
CA2355814C (fr) * 2000-09-14 2010-06-29 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Composition pharmaceutique pour utilisation ophthalmologique
US6562600B1 (en) * 2001-06-25 2003-05-13 The United States Of America As Represented By The Secretary Of Agriculture Production of cyclic alternan tetrasaccharides from oligosaccharide substrates
KR20030016706A (ko) * 2001-08-21 2003-03-03 주식회사 가릭솔 오동성분을 주원료로 하는 활성산소 제거제 및 그 제조방법
JP4397142B2 (ja) * 2001-11-20 2010-01-13 株式会社林原生物化学研究所 活性酸素消去能低減抑制剤
US20050065030A1 (en) * 2001-11-20 2005-03-24 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Reduction inhibitory agent for active oxygen eliminating activity

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0868916A2 (fr) * 1997-03-04 1998-10-07 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Agent-inhibiteur de la réduction pour l'activité d'élimination d'oxygène actif
EP1284286A1 (fr) * 2000-05-22 2003-02-19 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Alpha-isomaltosyltransferase, procede de production et utilisation
EP1229112A1 (fr) * 2000-08-01 2002-08-07 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Synthase d'alpha-isomaltosylglucosaccharide, procede de preparation et utilisation associes

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BIELY P ET AL: "Enzymic alpha-galactosylation of a cyclic glucotetrasaccharide derived from alternan", CARBOHYDRATE RESEARCH, ELSEVIER SCIENTIFIC PUBLISHING COMPANY. AMSTERDAM, NL, vol. 332, no. 3, 4 June 2001 (2001-06-04), pages 299 - 303, XP004249620, ISSN: 0008-6215 *
BRADBROOK G M ET AL: "X-ray structure determination and modeling of the cyclic tetrasaccharide cyclo-{->6)-alpha-d-Glcp-(1->3)-alpha-d-Glcp-(1->6)-a lpha-d-Glcp-(1->3)-alpha-d-Glcp-(1- >}", CARBOHYDRATE RESEARCH, ELSEVIER SCIENTIFIC PUBLISHING COMPANY. AMSTERDAM, NL, vol. 329, no. 3, 17 November 2000 (2000-11-17), pages 655 - 665, XP004221215, ISSN: 0008-6215 *
COTE G L ET AL: "ENZYMICALLY PRODUCED CYCLIC ALPHA-1,3-LINKED AND ALPHA-1,6-LINKED OLIGOSACCHARIDES OF D-GLUCOSE", EUROPEAN JOURNAL OF BIOCHEMISTRY, BERLIN, DE, vol. 226, 1994, pages 641 - 648, XP002945423, ISSN: 0014-2956 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100943559B1 (ko) * 2001-11-20 2010-02-22 가부시끼가이샤 하야시바라 세이부쓰 가가꾸 겐꾸조 활성산소 소거능 저감 억제제
WO2004020552A1 (fr) * 2002-08-30 2004-03-11 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Inhibiteurs de reactions radicalaires, procede d'inhibition de reactions radicalaires et utilisation associee
EP1541660A1 (fr) * 2002-08-30 2005-06-15 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Inhibiteurs de reactions radicalaires, procede d'inhibition de reactions radicalaires et utilisation associee
EP1541660A4 (fr) * 2002-08-30 2007-08-01 Hayashibara Biochem Lab Inhibiteurs de reactions radicalaires, procede d'inhibition de reactions radicalaires et utilisation associee
EP1652527A1 (fr) * 2003-07-18 2006-05-03 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Accelerateur d'absorption minerale et utilisation associee
EP1652527A4 (fr) * 2003-07-18 2012-03-14 Hayashibara Biochem Lab Accelerateur d'absorption minerale et utilisation associee
CN108617757A (zh) * 2018-03-27 2018-10-09 荔浦县万家兴果蔬专业合作社 一种葡萄的保鲜方法

Also Published As

Publication number Publication date
TW200300331A (en) 2003-06-01
JP4397142B2 (ja) 2010-01-13
DE60211632D1 (de) 2006-06-29
US20050123671A1 (en) 2005-06-09
KR100943559B1 (ko) 2010-02-22
JP2003160495A (ja) 2003-06-03
US20030108593A1 (en) 2003-06-12
DE60211632T2 (de) 2007-05-10
TWI256292B (en) 2006-06-11
KR20030041813A (ko) 2003-05-27
EP1321148B1 (fr) 2006-05-24

Similar Documents

Publication Publication Date Title
US7186824B2 (en) Reduction inhibitory agent for active-oxygen eliminating activity
EP1321148B1 (fr) Utilisation de cyclotetrasaccharides pour augmenter l'activité d'élimination de l'oxygène actif
US20090110671A1 (en) Agent for enhanching the production of collagen and it's use
EP1679071A1 (fr) Activateur de la production de collagene et procede de production et d'utilisation de celui-ci
JP4520386B2 (ja) ニンニクから得られる発酵物
EP2145615A1 (fr) Agent d'éclaircissement de la peau contenant un composé d'équol en tant que principe actif
KR0156539B1 (ko) 4지-o-알파-디이-글루코피라노실 루틴 및 그 제조 방법
WO2004060077A1 (fr) Procede de reduction d'un gout desagreable et/ou d'une odeur desagreable
US20070218189A1 (en) Reduction inhibitory agent for active oxygen eliminating-activity
JP4492956B2 (ja) アセロラ発酵物
KR101075696B1 (ko) 휘발성 알데히드류의 생성 및/또는 지방산류의 분해를 억제하는 방법과 그 용도
JP4624742B2 (ja) シソの葉から得られる発酵物
JP4363841B2 (ja) ポリフェノールの水に対する溶解性の改善方法ならびにポリフェノール高含有水溶液
JP2006076925A (ja) トマトから得られる発酵物
JP2010265215A (ja) メチオニナーゼ阻害剤
JP2006075083A (ja) ゴーヤから得られる発酵物
JPH11263795A (ja) 活性酸素消去能低減抑制剤
JPH0763294B2 (ja) 抗う蝕性食品
JP2006089408A (ja) レモンから得られる発酵物
JP3014128B2 (ja) 抗う蝕剤および抗う蝕性物質の製造方法
JP2004269488A (ja) 結晶α−D−グルコシルα−D−ガラクトシドとこれを含有する糖質及びこれらの製造方法並びに用途
JP2006076926A (ja) ピーマンから得られる発酵物
JP2006087345A (ja) ナスから得られる発酵物
RU2317299C2 (ru) Ассоциат, содержащий трегалозу и хлорид кальция, в форме кристаллического моногидрата или безводного кристалла

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LI LU MC NL PT SE SK TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

17P Request for examination filed

Effective date: 20030707

AKX Designation fees paid

Designated state(s): DE FR GB

17Q First examination report despatched

Effective date: 20040809

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

RIC1 Information provided on ipc code assigned before grant

Ipc: 7A 23B 7/154 A

RTI1 Title (correction)

Free format text: USE OF CYCLOTETRASACCHARIDE FOR AUGMENTING "ACTIVE-OXYGEN-ELIMINATING-ACTIVITY"

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE FR GB

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REF Corresponds to:

Ref document number: 60211632

Country of ref document: DE

Date of ref document: 20060629

Kind code of ref document: P

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed

Effective date: 20070227

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 14

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20161017

Year of fee payment: 15

Ref country code: DE

Payment date: 20161116

Year of fee payment: 15

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 16

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 60211632

Country of ref document: DE

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20171119

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 17

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20180602

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20171119

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20181026

Year of fee payment: 17

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20191130